The manual includes the following:

To keep the overview over the fraction of subtasks that are already completed, insert either ‘[/]’ or ‘[%]’ anywhere in the headline. These cookies will be updates each time the todo status of a child changes. For example:
     * Organize Party [33%]
** TODO Call people [1/2]
*** TODO Peter
*** DONE Sarah
** TODO Buy food
** DONE Talk to neighbor
This seems to mean that if I enter the following into an org file:
** TODO test3 [/]
*** TODO test 1
*** TODO test 2
*** TODO test 3
the [/] should be updated as I mark the sub tasks done. This doesn't work for me.

I can get [/] and [%] to work with checkboxes. Is there some variable that I need to set to get this to work?

Dave Ellis